I will be going to Chicago for the 4th of July weekend and need some super comfortable, yet stylish shoes, good for a lot of walking, and under $50!
I'd prefer sandals, or something that I won't have to wear socks with since it's going to be fairly warm.

Does anybody have any suggestions?

I'd suggest e.g. an Aerosoles brand, known for comfort, and choose a cute flat that can be paired with jeans / shorts etc for daytime wear, as well as convert pretty acceptably into evening. Some examples attached below that I really like, and all for sock-less wearing. Otherwise, for more sporty-chic, the Teva line is great and ultra comfortable.

(Found all of them on Shoebuy.com, where you can search by 'Comfort' and Price, with lots of options in your price range -- all of the above are under $50!)

OK, I am about to commit a fashion crime here. But in my defense, one of my former bosses at iVillage used to wear these and she was super chic (and this was in London, too...)

I love these Birkenstocks because they do not look like Birkenstocks. They are cute and white (they come in pink and blue too - and they used to have gold which was my favorite), they look much more summery and fun than the association of bratwurst and drudgery that Birkenstocks usually conjure up - at least in my mind.

These are a little more than your budget, but under $100.00 - and they will indeed last you a lifetime, so there is value in this purchase.

Just remember your pedicure - people will be staring at your feet trying to figure out where those cute but suspiciously comfortable shoes came from!!

Here is where you can buy them: http://www.zappos.com/product/7322386/color/87908

I have never ever seen a Birkenstock look cute...but that one does. Out of my size at Zappos...I'll have to do some investigation elsewhere lol

I personally love Geox....I have a pair and they are certainly my super serious walking shoes, and they have really comfortable/stylish sneakers, loafers, and more dressier..sandals that I swear you can actually walk in...